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A-D-A type conjugated molecules based on substituted indenothiophene condensed ring unit and preparation method thereof

A conjugated molecule, A-D-A technology, used in electrical components, semiconductor/solid-state device manufacturing, photovoltaic power generation, etc., can solve the problems of insufficiency of devices, low photoelectric conversion efficiency, etc., and achieve a wide absorption wavelength range, high photoelectric conversion efficiency, good solubility

Active Publication Date: 2017-03-29
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, the new energy of most small molecule materials still cannot meet the requirements of devices, and the photoelectric conversion efficiency is not high.

Method used

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  • A-D-A type conjugated molecules based on substituted indenothiophene condensed ring unit and preparation method thereof
  • A-D-A type conjugated molecules based on substituted indenothiophene condensed ring unit and preparation method thereof
  • A-D-A type conjugated molecules based on substituted indenothiophene condensed ring unit and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1: the synthesis of compound 5:

[0033] The synthetic route is as follows:

[0034]

[0035] Synthetic route of Scheme.1 compound 5

[0036] (1) Synthesis of Compound 3:

[0037] Add 9.3g of 4-bromo-phenylhexyl ether under the protection of nitrogen, dissolve it in 60ml of dry tetrahydrofuran, drop the temperature to -78°C, add 18ml of 2.0M butyl lithium dropwise, keep stirring at low temperature for 1 hour after dropping, and then add 3g of compound a dropwise 60ml of tetrahydrofuran solution, keep stirring at -78°C for 1 hour after dripping, monitor by TLC, add water to stop the reaction after the reaction is complete, extract, wash, spin off the solvent, the product obtained is recrystallized with ethanol, and then the light yellow solid is directly added to Glacial acetic acid 50ml and H 2 SO 4 Stir in 1ml of the system for 4h to terminate the reaction and recrystallize to obtain 4.5g of compound 3 with a yield of 70%. 1 H NMR (500MHz, CDCl 3 ),...

Embodiment 2

[0044] Embodiment 2: the synthesis of compound 9

[0045] The synthetic route is as follows:

[0046]

[0047] Synthetic route of Scheme.2 compound 9

[0048] (1) Synthesis of Compound 7

[0049] Add 9.3g of 3-bromo-phenylhexyl ether under the protection of nitrogen, dissolve it in dry tetrahydrofuran, drop the temperature to -78°C, add 18ml of 2.0M butyl lithium dropwise, stir for 1 hour after dropping, then add dropwise 3g of compound a in tetrahydrofuran 60ml, keep stirring at -78°C for 1 hour after dripping, monitor by TLC, add water to stop the reaction after the reaction is complete, extract, wash, and spin off the solvent. The product obtained is recrystallized with ethanol, and then the beige solid is directly added to 50ml of glacial acetic acid and H 2 SO 4 Stir in 1ml of the system for 4h, terminate the reaction and recrystallize to obtain 4.1g of compound 7 with a yield of 63%. 1 H NMR (500MHz, CDCl 3 ),7.51(s,2H),7.25(s,2H),7.16(t,J=10Hz,4H),6.84(m,8H),6...

Embodiment 3

[0056] Embodiment 3: the synthesis of compound 13

[0057] The synthetic route is as follows:

[0058]

[0059] Synthetic route of Scheme.3 compound 13

[0060] (1) Synthesis of Compound 11:

[0061] Add 9.9g of 2-fluoro-4-bromo-phenylhexyl ether under the protection of nitrogen, dissolve in 60ml of dry tetrahydrofuran, drop the temperature to -78°C, add 18ml of 2.0M butyllithium dropwise, stir for 1 hour after dropping, and then dropwise add 2 , Ethyl 5-bis(2-thiophene[3,2-b]thienyl)phthalate 3g / tetrahydrofuran 60ml, keep stirring at -78°C for 1 hour after dropping, monitor by TLC, stop the reaction after the reaction is complete, Extraction, washing, drying, concentration of solvent, recrystallization and suction filtration to obtain solid product, directly add glacial acetic acid 50ml and H 2 SO 4 1 ml was stirred for 4 hours to terminate the reaction, and recrystallized after suction filtration and washing to obtain 4.5 g of product 11 with a yield of 65%. 1 H NMR ...

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Abstract

The invention discloses A-D-A type conjugated molecules based on a substituted indenothiophene condensed ring unit, and a preparation method and an application of the molecules as an active layer material in organic photovoltaic device. The conjugated molecules have the structure represented by the following general formula defined in the specification. Different electrical absorption units alkoxy, fluorine atoms and the like are introduced to an indenothiophene condensed ring unit, the electron withdrawing characteristic of the fluorine atoms and the alkoxy is utilized, the HOMO energy level of the material is adjusted, then the open-circuit voltage of a photovoltaic battery is adjusted, the spectral absorption range is improved, and thus the photoelectric conversion efficiency of the device is improved.

Description

technical field [0001] The invention relates to an A-D-A type conjugated molecule based on a substituted indenothiophene condensed ring unit and a preparation method thereof, which is suitable for application as an active layer material in an organic photovoltaic (OPV) device. Background technique [0002] Organic solar cell is a kind of photoelectric device that converts solar energy into electrical energy. Its advantages of low cost, simple preparation process, light weight and flexible device have become one of the most active fields in photovoltaic research. Current research in this field The focus is to develop highly efficient donor and acceptor materials as photoactive layers for applications in devices to improve photoelectric conversion efficiency. At present, a large amount of research on the photoactive layer of photovoltaic cells focuses on the donor material, and the research on the acceptor material mainly focuses on fullerene and its derivatives, but fullerene...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22H01L51/42H01L51/46
CPCC07D495/22H10K85/6576H10K30/00Y02E10/549
Inventor 王维平高潮赵宝锋陈涛弥育华张杰刘红利
Owner XIAN MODERN CHEM RES INST
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